Ora and Rembert photographed April 27, 2014 at The Mercer in New York.

"I love working with musicians -- they’ll take risks,” says stylist Jason Rembert, elbows-deep in racks of the latest Emilio Pucci, Simone Rocha and Marni collections. “With an actress, you’re just doing pretty dresses.” It is a gusty spring afternoon, and Rembert, 26, is at the Karla Otto showroom in New York's West Chelsea nabe to select pieces for client Rita Ora, the British pop star whose songs are hits in England, but is better-known stateside for her bold fashion choices. The assignment: She had Rimmel press appointments -- having recently launched a capsule collection with the cosmetics brand -- and MTV upfronts the next day. Rembert triumphantly pulls out a gold, heavily sequined Pucci blazer and matching skinny trousers that might be part Prince, part Oscar statuette.

The same could be said of Rembert, despite his gentle, laid-back manner -- standing close to 6 feet, he almost has a huggable teddy bear vibe. In a few short years, his career has crackled, steering the red carpet images of Ora, Ciara and Iggy Azalea. He has persuaded Ora, who also works with stylist Kyle De’volle, to mix her London street style with more polished fare, such as the black plunging Barbara Casasola gown she wore to the recent MTV Movie Awards. But he also knows when to turn up the volume. “I love experimenting, and he has an eye to go wild and still be refined,” says Ora. “He’s definitely not afraid to tell me when I’ve gone too far, though.”

For Ciara, Rembert fine-tuned her minimalist aesthetic, while incorporating her pregnancy figure. Since he started working with her last fall, he has already dressed her, bump and all, in men's Lanvin, boho Naeem Khan and gold-beaded Pucci. “If I have a vision for something, he knows how to achieve it and take it to the next level,” says Ciara.

And with Azalea, Rembert skipped the raunchy body suits and bra tops (although still very much a part of the rapper¹s stage look) in favor of surprisingly soigne red carpet silhouettes. Azalea became a designer darling overnight, suddenly modeling high-necked Chloe separates and demure Elie Saab gowns as if she were a socialite. Earlier this year Rembert took on a broader role as the rapper¹s fashion consultant, suggesting labels with which she should be aligned.

Yet, if European designers now roll off his tongue, it wasn’t always his vernacular. A native of Queens' Jamaica and the middle child of five, Rembert describes his childhood as “hard” and underscored by poverty.

“Seeing so many people in my neighborhood struggle… I always wanted more,” he says.

By his third year of college at Hofstra University, he had found a way out: a coveted internship at Elle magazine. He remembers the experience as “scary” and a “wake-up call.” Recalls Rembert: “A lot of these young interns were privileged. I had support from my family, but my mom couldn’t afford to give me $13 every day to go to Cosi to eat.”

Intimidated or not, he was determined. By 2009, he had dropped out of college and moved on to internships with W magazine and the stylist Wouri Vice, who was then working with Alicia Keys. Rembert’s taste of the wild music-fashion scene would whet his appetite for more. Eventually, he landed his first client, Electrik Red, an R&B girl group on Def Jam, and later picked up jobs with rappers Wale and A$AP Rocky.

While on the set for Rocky’s “Street Knocks” video with Swizz Beatz, he got the call to style a young new talent: Ora. “I was like, I’m having the best week of my life,” he recalls with a chuckle.

Three years later, Rembert and Ora have hit a groove that’s nearly intuitive. “I can tell Jason a feeling I want to portray on the carpet and he can make that emotion come to life,” says Ora. It’s a dynamic that has paid off all around. Ora (as well as Ciara and Azalea) now frequents best-dressed lists, while Rembert has opened an office in Midtown Manhattan and travels the world for fashion shows.

But if his fabulous career ever gets overwhelming, Rembert says he finds perspective in Jamaica, where he still resides, “in the same home I lived in my whole life,” he says. “It’s grounding.”